(1R,2S,3S,5S)-3-(4-Thiophen-3-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester | 848469-63-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,2S,3S,5S)-3-(4-Thiophen-3-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester
• CAS: 848469-63-6
• 化学式: C₂₂H₂₂Cl₃NO₄S
• 分子量: 502.846
• InChiKey: JYKFILJQOJWTAT-MANSERQUSA-N

物化性质

• 沸点：
  552.0±50.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5S)-3-(4-Thiophen-3-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of new 2β-carbomethoxy-3β-[4-(substituted thiophenyl)]phenyltropanes: discovery of a selective SERT antagonist with picomolar potency

  摘要：

  Preparation of cocaine analogues has been aimed largely at development of stable compounds with high affinity and selectivity for the dopamine transporter (DAT). We now report the synthesis and monoamine transporter affinity of 10 new 2beta-carbomethoxy-3p-[4-(substituted thiophenyl)]phenyltropanes. Among these, compound 4b exhibited very high affinity for the serotonin transporter (SERT: K-i = 17 pM) and good selectivity over dopamine (DAT: 710-fold) and norepinephrine transporters (NET: 11,100-fold). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.014
• 作为产物：
  描述：

  (1R,2S,3S,5S)-3-(4-Iodo-phenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 (1R,2S,3S,5S)-3-(4-Thiophen-3-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of new 2β-carbomethoxy-3β-[4-(substituted thiophenyl)]phenyltropanes: discovery of a selective SERT antagonist with picomolar potency

  摘要：

  Preparation of cocaine analogues has been aimed largely at development of stable compounds with high affinity and selectivity for the dopamine transporter (DAT). We now report the synthesis and monoamine transporter affinity of 10 new 2beta-carbomethoxy-3p-[4-(substituted thiophenyl)]phenyltropanes. Among these, compound 4b exhibited very high affinity for the serotonin transporter (SERT: K-i = 17 pM) and good selectivity over dopamine (DAT: 710-fold) and norepinephrine transporters (NET: 11,100-fold). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.014